Ex-Maple Leafs GM Kyle Dubas shares his "biggest mistake" involving Auston Matthews, Mitch Marner and $92,000,000 star

Former Toronto Maple Leafs GM Kyle Dubas had negotiated Mitch Marners’ six-year contract in 2019. He struggled to secure team-friendly deals for the key players, often paying above market value, as the negotiations frequently extended to the last possible moment. Dubas seems aware of this legacy.

In Craig Custance’s upcoming book, The Franchise: The Business Of Building Winning Teams, Dubas admitted his biggest regret. The book will be released in October 2024.

"The biggest mistake I think I’ve made in my whole time here has been not taking care of the three incumbent contracts," Dubas said. "William Nylander was up, Mitch Marner and Auston Matthews could have been done on July 1 extensions."

Nylander's contract was signed at the last minute, a six-year, $41.4 million extension in 2018. Marner briefly held out before signing his long-term deal in September 2019. These incidents pointed to Dubas’ challenges in contract negotiations. On Jan. 8, Nylander signed an eight-year, $92 million contract with the Leafs. On Aug. 23, 2023, Auston Matthews signed a four-year contract worth $53 million.

Critics often said Dubas' roster-building was too top-heavy. While neither Dubas nor the Maple Leafs regret pursuing John Tavares, there is a lesson here. Timely contract agreements are beneficial for the team.

Dubas became president of hockey operations for the Pittsburgh Penguins in June 2023, bringing Jason Spezza with him. Wes Clark, Toronto’s former head scout, joined the Penguins earlier this week. Dubas has learned so many things in his time with Leafs and he will probably try to handle the Penguins' contract situation by not replicating his mistakes.

Mitch Marner's future is uncertain as his contract year begins

Mitch Marner is staying with the Toronto Maple Leafs, at least for now. After trade rumors circulated following their playoff exit, Marner, entering the final year of his contract, seems set to start the season with Toronto. Despite speculation, he holds a no move clause, giving him control over any potential trade.

NHL insider Chris Johnston said Marner walking in free agency is more likely than a trade or extension, though staying remains an option.

On July 9, Johnston said, via the SDPN podcast:

“It’s probably slightly more likely he walks than signs an extension but not significantly so. If we were setting the betting lines now the favorite would be (he) walks as a free agent."

Mitch Marner's future with the Maple Leafs, who drafted him fourth overall in 2015, hinges on upcoming contract negotiations and team decisions leading into the new season.